86795-60-0

Upstream product

• 118-48-9 isatoic anhydride 
• 17281-71-9 pyridinium bis(ethoxycarbonyl)methylide 
• 87-25-2 2-ethoxycarbonylaniline 
• 86795-59-7 1-(4-Hydroxy-2-oxo-1,2-dihydrochinolin-3-yl)-pyridinium-iodid 
• 6307-66-0 2-(Chloracetylamino)benzoesaeure-ethylester 
• 110-86-1 pyridine 

Downstream Products

• 184536-33-2 tridecanoic acid (4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-amide 
• 184536-46-7 3-chloro-N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-benzamide 
• 184536-40-1 N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-3-methyl-benzamide 
• 184536-42-3 2-fluoro-N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-benzamide 
• 184536-48-9 2-bromo-N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-benzamide 
• 184536-44-5 2-chloro-N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-benzamide 
• 184536-50-3 4-bromo-N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-benzamide 
• 184536-38-7 N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-4-methyl-benzamide 
• 184536-35-4 N-(4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-2-phenyl-acetamide 
• 184536-36-5 3-benzoilaminoquinoline 
• 174197-07-0 2-Methyl-oxazolo[4,5-c]chinolin-4(5H)-on 

Relevant academic research and scientific papers

Ylides of Heterocycles, IV. Sulfonium- and Pyridinium-Ylides of Coumarin and 2-Quinolone

The title compounds 3 can be prepared either from the iodonium-ylides 1 or from the chlorocompounds 4.On treatment with hydrochloric acid the thiophanium-ylides 3C undergo ring cleavage to the chlorobutylsulfides 5, also formed from 4 and thiophane.The dimethylsulfonium-ylide 8 is derived from activated DMSO and 7b.The Ortoleva-King reaction is discussed as an alternative method for preparing pyridiniumylides. - Keywords: Activated dimethylsulfoxide; Ortoleva-King reaction; 2-Oxobenzopyran-4-olates; 2-Oxoquinolin-4-olates; Thiophanium ylides

Synthesis of Hetaryl Pyridinium Salts and Fused 3-Amino-pyrid-2-ones

1-(3-Coumaryl)-pyridinium salts 3 and 1-(3-coumaryl)-tetrahydrothiophenium salts 5 were synthesized from 2-acylphenyl chloro- or bromoacetates 2. 2-Chloro-N1-(3,4-dimethoxyphenyl)-acetamide and substituted 2-chloro-N1-(2-thienyl)-acetamides 8 react with acetyl chloride and pyridine to yield the quinolinyl- and (thieno[2,3-b]pyridin-5-yl)-pyridinium salts 10. Fused thieno[2,3-b]pyridin-ones 19 were formed from N-chloroacetyl-2-aminothiophen-3-carbonitriles 16 with pyridine via Thorpe-Ziegler cyclization and followed by cyclodehydrogenation. In presence of pyridine alkyl 2-chloro-acetylaminobenzoates 21 yield 3-(1-pyridinio)-quinoline-4-olates 23. Zincke-cleavage of 10 and 23 with hydrazinium hydroxide leads to fused 3-amino-pyridine-2-ones 11 and 3-amino-4-hydroxy-quinoline-2-ones 24, respectively. Oxazoloquinolines 25 were synthesized from 24 with acetic anhydride.

4-hydroxy-2-quinolones. 31. 3-amino-1R-2-oxo-4-hydroxyquinolines and their acyl derivatives

An alternative method has been developed for preparing and studying the antioxidant activity of 3-acylamino-2-oxo-4-hydroxyquinolones. Results are presented from an investigation of the antithyroid and antimicrobial action of the intermediate 2-oxo-3-(1-pyridinio)quinolin-4-olates and the 3-amino-2-oxo-4-hydroxyquinolines. 1997 Plenum Publishing Corporation.

Ylides of Heterocycles, VIII. Reactions of Iodonium-Ylides with Acids

The reaction of various organic and inorganic acids (HX) with iodonium ylides 2 leads to nucleophilic substitution of the iodobenzene substituent by the anion X(-) to yield the heterocycles 5.Some of them are hydrolyzed to the hydroxy compounds 3 or reduced to the starting compounds 1 under the reaction conditions.Reaction of the iodonium ylide 2b with monomethyl sulfate gives the salt 9, which with bases undergoes nucleophilic substitution to compounds 8 and 10-12, respectively, or is converted to 2b again. - Keywords: 3-Acetoxy-4-hydroxy-2-quinolones; 2-Oxoquinoline-4-olates; 3-Substituted 4-hydroxy-2-quinolones

Ylides of Heterocycles, III. Pyridinium Ylides of Malonylheterocycles

Reaction of isatoic anhydride with the betaine esters 2 or 3 represents a new synthesis of pyridinium ylides of type 5, which have been previously obtained by several other ways.Treatment of the ylide 5 with inorganic acids results in the formation of their pyridinium salts 5a-d.Hydrogenation or dehydrogenation of 5 with Pd/C give the piperidylquinoline 9 or the betaine 10, respectively.Both of them can be prepared by an alternative way.The pK values of some pyridinium ylides were determined. - Keywords: Cyclodehydrogenation; Isatoic anhydride; Palladium; pK Values; Pyridiniummalonate betaine; Pyridinium ylides of quinolinediones